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Chapter 14: Q6P (page 527)

Question: Label the protons in each highlighted \({\bf{C}}{{\bf{H}}_{\bf{2}}}\) group as enantiotopic, diastereotopic, or homotopic.

a.

b.

c.

Short Answer

Expert verified

  1. Enantiotopic

  2. Neither

  3. Diastereotopic

Step by step solution

01

Homotopic, enantiotopic, and diastereotopic protons

  • Homotopic protons are formed when the same product is formed by the substitution of two H by Z.
  • Enantiotopic protons are formed when two H are equivalent and occur at the same NMR signal.
  • Diastereotopic protons are formed when two H are not equivalent and occur at two different signals.
02

Explanation for highlighted proton

a.

The replacement of H with X is shown below.

Enantiotopic proton

b.

The replacement of H with X is shown below.

Neither enantiotopic nor diastereotopic

c.

The replacement of H with X is shown below.

Diastereotopic proton

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Most popular questions from this chapter

Compound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate and which compound corresponds to ethylene diacetate?

Explain why the carbonyl carbon of an aldehyde or ketone absorbs farther downfield than the carbonyl carbon of an ester in a \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum

Which of the highlighted carbon atoms in each molecule absorbs farther downfield?

a.

b.

c.

d.

Question: The \(^{\bf{1}}{\bf{H}}\) NMR spectrum of \({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{OH}}\) recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the \({\bf{C}}{{\bf{H}}_{\bf{3}}}\) protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the \({\bf{C}}{{\bf{H}}_{\bf{3}}}\) protons absorb upfield or downfield from the OH proton?

Label each statement as True or False.

a. When a nucleus is strongly shielded, the effective field is larger than the applied field and the absorption shifts downfield.

b. When a nucleus is strongly shielded, the effective field is smaller than the applied field and the absorption is shifted upfield.

c. A nucleus that is strongly deshielded requires a lower field strength for resonance.

d. A nucleus that is strongly shielded absorbs at a larger δ value.
See all solutions

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